Rubrofusarin B

ID: ALA469613

Cas Number: 17276-15-2

PubChem CID: 176918

Max Phase: Preclinical

Molecular Formula: C16H14O5

Molecular Weight: 286.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(O)c3c(=O)cc(C)oc3cc2c1

Standard InChI:  InChI=1S/C16H14O5/c1-8-4-11(17)15-13(21-8)6-9-5-10(19-2)7-12(20-3)14(9)16(15)18/h4-7,18H,1-3H3

Standard InChI Key:  HFPQKJMLIONCGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -1.5256   -1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274    0.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406   -0.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365    0.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587    0.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -0.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515   -1.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141    0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131   -0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -1.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6213   -0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162    0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018    0.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -1.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -2.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065    1.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322    1.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9380    1.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799   -1.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    1.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
  9  2  2  0
 11 12  2  0
  2  4  1  0
 12 13  1  0
  3  4  2  0
 13 14  2  0
 14  9  1  0
  3  8  1  0
 12 15  1  0
  4  5  1  0
 15 16  1  0
  5  6  1  0
 14 17  1  0
  6  7  2  0
  2 18  1  0
  7  8  1  0
  5 19  2  0
  3  1  1  0
  7 20  1  0
  1 10  2  0
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA469613

   RUBROFUSARIN B

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 286.28

Molecular Weight (Monoisotopic): 286.0841

AlogP: 2.98

#Rotatable Bonds: 2

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.82

CX Basic pKa: ┄

CX LogP: 2.89

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 1.44

References

1. Ye YH, Zhu HL, Song YC, Liu JY, Tan RX..  (2005)  Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFB-E002.,  68  (7): [PMID:16038560] [10.1021/np050059p]

2. Macías M, Ulloa M, Gamboa A, Mata R..  (2000)  Phytotoxic compounds from the new coprophilous fungus guanomyces polythrix.,  63  (6): [PMID:10869195] [10.1021/np990534h]

3. Zhou X, Fang W, Tan S, Lin X, Xun T, Yang B, Liu S, Liu Y..  (2016)  Aspernigrins with anti-HIV-1 activities from the marine-derived fungus Aspergillus niger SCSIO Jcsw6F30.,  26  (2): [PMID:26711143] [10.1016/j.bmcl.2015.12.005]

4. Carter AC, King JB, Mattes AO, Cai S, Singh N, Cichewicz RH..  (2019)  Natural-Product-Inspired Compounds as Countermeasures against the Liver Carcinogen Aflatoxin B₁.,  82  (6): [PMID:31136174] [10.1021/acs.jnatprod.9b00290]

5. Hu YW, Liu Y, Guo EY, Wang YY, Xu WQ, Gao Y, Jiang XY, Feng F, Xu J, Liu WY..  (2021)  Naphtho-γ-pyrone Dimers from an Endozoic Aspergillus niger and the Effects of Coisolated Monomers in Combination with Cisplatin on a Cisplatin-Resistant A549 Cell Line.,  84  (7.0): [PMID:34156846] [10.1021/acs.jnatprod.0c01262]

Source

Source(1):

• Scientific Literature